Vacation Checklist: 4 Steps to Prepare for Your Time Off

Summer is almost over, which means that cubicle-dwellers everywhere are packing their bags and trying to squeeze in a little more vacation time before the weather turns chilly.

But before you ditch your high heels for flip-flops, remember to tie up any loose ends at work. By making sure that your schedule is clear and your work is done before you leave, you can focus on the really important stuff while you’re away—like choosing between a piña colada and a strawberry daiquiri.

Here’s what you need to do to make sure your time off from work is a success.

A Few Months Before: Get It On the Calendar

A friend of mine recently saved up for months to go to South Africa, only to learn that he’d have to return early to attend a critical work event—and buy a new $1,200 plane ticket home to replace his original, non-refundable flight. The moral of this story? Before you book your tickets or pay for a single hotel room, run your vacation plans past your boss. Make sure that your absence won’t coincide with major meetings, can’t-miss conferences, or any other big events.

While you’re at it, double check that you have enough PTO or vacation time to cover the trip you’re planning. It’s an easy step to take, and it can save you a lot of money spent on cancelled plans and lost vacation deposits (not to mention a lot of heartache) if for any reason you can’t take time off.

A Couple Weeks Before: Work Ahead

Make a list of what you need to accomplish before you leave, as well of any projects that need to be completed as soon as you get back from vacation. Share this list with your boss ahead of time as well, so you’re on the same page about what’s going to be done before you leave and what you’ll finish when you return.

Then, work ahead to make sure that everything on that list is wrapped up before your trip arrives—even if it means eating lunch at your desk or spending a few late nights at the office. You don’t want to miss out on the vacation fun because you’re worrying about upcoming deadlines, or—even worse—stuck in your hotel room finishing projects on your laptop.

You may even want to recruit a coworker to help carry your workload and take care of any critical projects that pop up while you’re away. Just make sure that your boss is okay with you delegating the work, and remember to give your co-worker all the info he or she needs to complete the project. Include a detailed list of instructions, the project’s deadline, and a way to contact you if problems or questions arise.

The Week Before: Discuss How Disconnected You Will Be

In an ideal world, packing for a vacation would be simple. Swimsuit—check. Sunscreen—check. Laptop—not necessary. Unfortunately, the reality is that many of us can’t afford to totally disconnect from work for a week or more. Before you leave for vacation, ask your boss if she expects you to check emails or listen to voice messages while you’re gone. If you’re going to be in a location without cell phone reception or Wi-Fi, make sure that your boss knows that she won’t be able to reach you.

And while it’s often necessary to stay at least a little connected, make sure you proactively set some boundaries. Feel free to let your boss know that you’ll only be able to check your phone and email occasionally—say, once a day, or a few times a week. Most bosses will be fine if you only respond to critical messages until after you return to the office.

Setting expectations ahead of time can be a major money-saver (cell phone out-of-network charges can add up fast), and, more importantly, ensures that you’ll get to spend the bulk of your time relaxing—not just working remotely.

The Day Before: Say Your Goodbyes

Vacations are a great way to relax and recharge, but they’re not an excuse to let good manners fall by the wayside. Be sure to let clients and co-workers know in advance that you’ll be out of town, tell them when you plan to return, and give them the name of whomever they should contact with questions or concerns in the meantime. You’ve worked hard to cultivate good relationships with your co-workers and customers. The last thing that you want to do is make them wonder where you’ve gone or why they’re being ignored.

Finally, right before you head out the door, change the message on your phone and set the out-of-office reminder on your work email so that anyone trying to contact you while you’re away knows when you’ll be back and who to contact in the meantime.

The next time you get ready to leave work for a few days, make sure that you’ve completed this pre-vacation checklist. It’ll help keep your vacation stress-free and let you spend at least a few days this summer enjoying life’s simple pleasures—without worrying about what’s going on back at the office.

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Lynze Wardle Lenio is a freelance journalist from Salt Lake City, Utah. When she’s not investigating workplace relationships, she enjoys skiing and traveling with her husband. You can follow her adventures at home and abroad at www.thetravelogueblog.com.